In asymmetric reduction, asymmetric isomerization and the like using a transition metal coordinated with optically active phosphine as a catalyst, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (hereinafter, abbreviated as BINAP in some cases) is generally used as the optically active phosphine. However, reactions using BINAP may be poor in reactivity, stereoselectivity, catalyst efficiency or the like depending on the kind of a substrate. Therefore various optically active phosphines have been prepared and reported (e.g., see Handbook of Enantioselective Catalysis with Transition Metal Compounds, published by VCH in 1993). For example, JP-A 61-63690 discloses that a ruthenium complex with 2,2′-bis(di(p-tolyl)phosphino)-1,1′-binaphthyl as a ligand is useful for asymmetric reduction of a carbon-carbon double bond. JP-A 3-255090 discloses that a ruthenium complex with 2,2′-bis(di(3,5-dialkylphenyl)phosphino)-1,1′-binaphthyl as a ligand is useful for asymmetric reduction of β-ketoester.
However, reactions using these transition metal catalysts may be poor in optical selectivity in some cases depending on a reaction substrate.